CN1875323B - Thick film or ultrathick film responsive chemical amplification type photosensitive resin composition - Google Patents
Thick film or ultrathick film responsive chemical amplification type photosensitive resin composition Download PDFInfo
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- CN1875323B CN1875323B CN2004800319435A CN200480031943A CN1875323B CN 1875323 B CN1875323 B CN 1875323B CN 2004800319435 A CN2004800319435 A CN 2004800319435A CN 200480031943 A CN200480031943 A CN 200480031943A CN 1875323 B CN1875323 B CN 1875323B
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- China
- Prior art keywords
- photosensitive resin
- resin composition
- alkali
- acid
- film
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 74
- 239000000126 substance Substances 0.000 title claims description 24
- 238000003199 nucleic acid amplification method Methods 0.000 title description 11
- 230000003321 amplification Effects 0.000 title description 9
- 239000003513 alkali Substances 0.000 claims abstract description 45
- 239000002253 acid Substances 0.000 claims abstract description 43
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 33
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 229920003986 novolac Polymers 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 14
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 11
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 11
- -1 alkyl methacrylate Chemical compound 0.000 claims description 46
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- DUTKISIXBXRUCA-UHFFFAOYSA-N 3,6,11-trioxabicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-2,12-dione Chemical compound C1(C2=CC(C(=O)OCCCCOCCO1)=CC=C2)=O DUTKISIXBXRUCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005591 trimellitate group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 12
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 6
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 31
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 21
- 238000007747 plating Methods 0.000 description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 239000000178 monomer Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229920002120 photoresistant polymer Polymers 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 239000011354 acetal resin Substances 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920006324 polyoxymethylene Polymers 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical class N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 230000004304 visual acuity Effects 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002438 flame photometric detection Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229940100630 metacresol Drugs 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 2
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 2
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- 238000009833 condensation Methods 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
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- 125000001188 haloalkyl group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
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- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- SHMWGXIEPCHLGC-UHFFFAOYSA-N (4-ethenylphenyl)-phenylmethanone Chemical compound C1=CC(C=C)=CC=C1C(=O)C1=CC=CC=C1 SHMWGXIEPCHLGC-UHFFFAOYSA-N 0.000 description 1
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- DSIWLDCXHHMNQL-UHFFFAOYSA-N 2-ethenyl-1,4-difluorobenzene Chemical compound FC1=CC=C(F)C(C=C)=C1 DSIWLDCXHHMNQL-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
Abstract
This invention provides a chemically amplified photosensitive resin composition suitable for forming a thick film and a super thick film, which has high sensitivity, high film residual properties, good coating properties, high resolution and a good pattern shape, and which gives a pattern excellent in heat resistance, in a photosensitive resin composition requiring the formation of a thick resist pattern film such as in the formation of a magnetic pole of a magnetic head or of a bump. A chemically amplified photosensitive resin composition including an alkali soluble novolak resin (A), a resin or compound (B) which in itself is insoluble or slightly soluble in alkali, but becomes soluble in alkali by the action of an acid, that is acid generating agent (C), and a photosensitizing agent (D) containing a quinonediazide group, as well as, if necessary, an alkali soluble acrylic resin (E) and a crosslinking agent (F) for improving film quality.
Description
Technical field
The present invention relates to a kind of photosensitive resin composition, more particularly, relate to a kind of chemical amplification type photosensitive resin composition that is suitable for forming thick film and super thick film, these films can be used for producing the semiconductor devices suitably, flat-panel monitor (FPD), circuit board, magnetic head etc., and the magnetic pole and the formation that particularly can be used to form magnetic head suitably are known as the projection electrode (protruding electrode) (it is used as the connecting terminal of large scale integrated circuit (LSI)) of " projection ".
Background technology
Make as the display surface of LSI and so on SIC (semiconductor integrated circuit), FPDs etc. and make the wide spectrum of the circuit board that is used for thermal head etc. comprising, photoetching technique had been used up to now already, was used for forming microcomponent or realization retrofit.In photoetching technique, use the photosensitive resin composition of positivity or negativity to form corrosion-resisting pattern.In these photosensitive resin compositions, adopt widely contain alkali soluble resins and as the composition of the quinone di-azido compound of photosensitizer as the positive light-sensitive resin combination.As for these compositions, multiple composition for example is described to " novolac resin/quinone di-azido compound " in many documents (for example, referring to following patent documentation 1～4).These contain the composition of novolac resin and quinone di-azido compound, study from the angle of novolac resin and quinone di-azido compound already.
Patent documentation 1: Japanese Patent Application (JP-B) 54-23570 (the 1st page)
Patent documentation 2:JP-B 56-30850 (the 1st page)
Patent documentation 3: Japanese Unexamined Patent Publication No (JP-A) 55-73045 (the 1st～4 page)
Patent documentation 4:JP-A 61-205933 (the 1st and 3～5 page)
Incidentally, need the field of thick film process at magnetic head, projection etc., it is essential forming the corrosion-resisting pattern with high aspect ratio and vertical wall.But the aforementioned conventional photoresist of mentioning exists problems, for example, can not fully keep perhaps, can not providing the corrosion-resisting pattern of wanting by resolution and the sensitivity that (owing to thickening of film) cause that descends of the optical transparency of film.Similarly, the improvement at these problems also needs.
As for the photosensitive resin composition that is used for dry film system (they can form the corrosion-resisting pattern with thick film thickness), hitherto known have: the photosensitive resin composition (referring to following patent documentation 5) that contains novolac resin, acetal compound (the acetal part that has repetition in its main chain, and each alpha-carbon atom of pure composition contains aliphatic carbons in its acetal part) and acid producing agent; Contain alkali soluble resins just like novolac resin and so on, acetal compound, acid producing agent and as the photosensitive resin composition (referring to following patent documentation 6) of the special additive of alkyl acrylate and so on; With the photosensitive resin composition that contains alkali soluble resins, acetal compound and acid producing agent (referring to following patent documentation 7) just like novolac resin and so on.In addition, the known photosensitive resin composition that contains acetal compound and acid producing agent also has: contain a kind of three kinds of not photosensitive resin compositions of novolac resin, acetal compound and the acid producing agent of phenol of the same race (referring to following patent documentation 8) that contain; Contain a kind of in its molecule, the have novolac resin of acetal bonds and the photosensitive resin composition of acid producing agent (referring to following patent documentation 9); With the photoresist (referring to following patent documentation 10) that contains novolac resin, acetal compound (chlorobenzene formaldehyde-hexichol oxygen ethyl acetals) and acid producing agent (2-alkoxyphenyl radical-4,6-two (trichloromethyl)-s-triazine).And; the photosensitive resin composition that is suitable for forming the resist layer with 10 μ m or thicker thickness or super thick degree (being suitable for forming projection) is disclosed; it is a kind of a kind of polymkeric substance that contains with acid disassociation functional group; the photosensitive resin composition of tygon lower alkyl ether and acid producing agent (referring to following patent documentation 11); the photosensitive resin composition of the thick etchant resist that is suitable for forming 3 μ m or thicker (being suitable for making magnetic head) is also disclosed; it is a kind of photosensitive resin composition (referring to following patent documentation 12) that contains alkali solubility novolac resin (wherein the part hydrogen atom of whole phenolic hydroxyl group is by 1, and 2-naphthoquinones two nitrine sulfonyls replace) and acid producing agent.But, for instance, in order to be fit to have the super thick film of 20～100 μ m film thicknesses, the stability that need have good pattern reproduction and change with respect to pattern form and the development time of exposure back standing time, and the high resolving power that forms meticulous right angle pattern with high aspect ratio, from the production cost angle, also require further improvement the thermotolerance and the turnout (yield of unit time) of gained pattern in the production run.Even be in this class situation, people still wish to be further improved at these problems.
Patent documentation 5:JP-A 53-133429 (the 1st～17 page)
Patent documentation 6:JP-A 57-37349 (the 1st～6 page)
Patent documentation 7:JP-A 58-114031 (the 1st～5 page)
Patent documentation 8:JP-A 62-124556 (the 1st～4 page)
Patent documentation 9:JP-A 62-215947 (the 1st and 3～5 page)
Patent documentation 10:JP-A 4-182650 (the 1st and 3～5 page)
Patent documentation 11:JP-A 2001-281863 (the 2nd and 4～9 page)
Patent documentation 12:JP-A 2001-312060 (2-7 page or leaf)
Summary of the invention
Consider the above situation, purpose of the present invention is to amplify at the chemistry that is fit to thick film and super thick film process to provide a kind of chemistry to amplify photosensitive resin composition in the photosensitive resin composition, it has high photosensitivity and high residue film character, and, it also has good coating character, have high resolving power, and can form good pattern, it can also give the gained pattern good thermotolerance.
Inventor's outdo oneself ground is studied and is detected, found that, the above purpose can be by for example surpassing the thick film process of 10 μ m or have the chemistry that thickness for example surpasses among the super thick film process of 20 μ m and amplify photosensitive resin composition will being used for having thickness, use a kind of specific light photosensitive resin composition and reach, thereby realization the present invention, this photosensitive resin composition contains the alkali solubility novolac resin, self is insoluble or be slightly soluble in alkali but resin or compound that effect by acid becomes and can be dissolved in alkali, by radiation irradiation energy acidic compound (it is an acid producing agent), with the photosensitizer that contains the quinone diazido.
In other words, the present invention relates to a kind of chemistry and amplify photosensitive resin composition, it contains alkali solubility novolac resin (A), self is insoluble or be slightly soluble in alkali but effect by acid becomes resin or compound (B), acid producing agent (C) that can be dissolved in alkali and the photosensitizer (D) that contains the quinone diazido, also relate to a kind of chemistry and amplify photosensitive resin composition, it is to obtain among aforementioned chemistry amplification photosensitive resin composition by the optional crosslinking chemical (F) that selectively adds alkaline soluble acrylic resin (E) and be used to improve film quality.
Hereinafter, will elaborate to the present invention.
Be used for the alkali solubility novolac resin (A) that the present invention's chemistry amplifies photosensitive resin composition, can be any one containing alkali soluble resins and containing the conventional known alkali solubility novolac resin that uses in the photosensitive resin composition of quinone diazido photosensitizer, be not particularly limited.Be used for novolac resin of the present invention preferably one or more potpourri and the aldehyde such as formalin by various phenol carry out that polycondensation obtains.
The example that constitutes the phenol of this class novolac resin comprises: phenol, paracresol, metacresol, orthoresol, 2, the 3-xylenols, 2, the 4-xylenols, 2, the 5-xylenols, 2, the 6-xylenols, 3, the 4-xylenols, 3, the 5-xylenols, 2,3,4-front three phenol, 2,3,5-front three phenol, 3,4,5-front three phenol, 2,4,5-front three phenol, the methylene bis-phenol, the di-2-ethylhexylphosphine oxide paracresol, resorcinol, catechol, the 2-methylresorcinol, cresorcinol, o-chlorphenol, m-Chlorophenol, parachlorophenol, 2, the 3-chlorophenesic acid, meta-methoxy phenol, p methoxy phenol, to butoxy phenol, o-ethyl phenol, m-ethylphenol, paraethyl phenol, 2, the 3-diethyl phenol, 2, the 5-diethyl phenol, australol, alpha-Naphthol, betanaphthol, or the like.These phenol can use separately, or use with multiple form of mixtures.In these phenol, use the combination of two or more phenolic compounds, as using two kinds of phenol simultaneously, metacresol and paracresol obtain more excellent result through regular meeting.
In addition, the example of aldehyde comprises: paraformaldehyde, acetaldehyde, benzaldehyde, hydroxy benzaldehyde, chloro acetaldehyde etc. and formalin.These aldehyde can use separately, or use with multiple form of mixtures.
Be used for the weight-average molecular weight that the present invention's chemistry amplifies the alkali solubility novolac resin (A) of photosensitive resin composition, preferably between 5000～100000, (record), more preferably 5000～50000 (recording) by polystyrene standard by polystyrene standard.
Be used for that the present invention chemistry amplifies described self insoluble or be slightly soluble in alkali but effect by acid becomes resin that can be dissolved in alkali of photosensitive resin composition or the example of compound (B) comprises acetal resin or acetal compound.Being used for aforementioned acetal resin of the present invention or acetal compound is not particularly limited, as long as they contain acetal resin or acetal compound, comprise the acetal compound described in the aforementioned patent document 5～10 shown in the prior art, but the acetal resin or the acetal compound that have the component units of following general formula (I) expression in molecular formula are preferred:
Wherein, R represents to have the alkyl of 1～20 carbon atom, and preferred expression has the saturated alkyl of 3～10 carbon atoms.More preferably the instantiation of alkyl comprises isopropyl, the tert-butyl group, 1-methyl-propyl and 1-ethyl propyl.N is 1～10 integer, is preferably 2～4.
In molecular formula, have the acetal resin of component units of general formula (I) expression or the mean molecular weight of compound, preferably between 100～10000,200～5000 (recording) more preferably by polystyrene standard.
As for acetal resin or the acetal compound by above-mentioned general formula (I) expression, the exemplary that can exemplify is the polycondensation product with repetitive of general formula (I) expression, and for example, it is by making aldehyde RCHO, glycol RCH (OH)
2, or acetal RCH (OR
1)
2(wherein, R represents the group of above-mentioned definition, and R
1The expression alkyl) polyglycol represented with ethylene glycol or by following general formula obtains reacting at 50 ℃ under reduced pressure in the presence of the acid catalyst:
Wherein, n represents the integer of above-mentioned definition.
Be used for that the present invention chemistry amplifies described self insoluble or be slightly soluble in alkali but effect by acid becomes resin that can be dissolved in alkali of photosensitive resin composition or the example of compound (B) also comprises this resinoid; they have by the decomposable blocking group of the effect of acid, and become alkaline soluble after decomposing by the effect of acid.Alkaline bleach liquor soluble alkali resin comprises that those have phenolic hydroxyl group and/or the carboxyl resin as the alkali solubility group before by the protection of aforementioned blocking group.Specifically, the example of this class alkali resin comprises: the vinyl benzene phenol resin; The isopropenylbenzene phenol resin; The multipolymer of vinylphenol, (methyl) acrylic acid or derivatives thereof, vinyl cyanide and styrene or derivatives thereof; The multipolymer of isopropenyl phenol, methacrylic acid or derivant, vinyl cyanide and styrene or derivatives thereof; The multipolymer of styrene or derivatives thereof and acrylate, methacrylate, acrylic acid, methacrylic acid, maleic acid, maleic anhydride etc.; Polymkeric substance or multipolymer with (methyl) acrylic acid derivative of carboxyl by using aforementioned (methyl) acrylic acid derivative to form as monomer as (methyl) acrylic acid; Be incorporated into resin among the above-mentioned polymer chain with silicon-containing compound.
Wherein at least a portion hydrogen atom of hydroxyl or carboxyl is by the alkali resin of decomposable blocking group institute modification under the acid effect, as resin of the present invention (B).As for blocking group, what can exemplify is the group that can form ethylidene ether structure, ether structure and ester structure with hydroxyl or carboxyl.The preferred embodiment of blocking group comprises 1-ethoxyethyl group, tertbutyloxycarbonyl and tert-butoxy ester group.
In the present invention, the described alkali solubility novolac resins of relative 100 weight portions (A), described self insoluble or be slightly soluble in alkali but effect by acid the becomes resin that can be dissolved in alkali or the common consumption of compound (B) are 1～50 weight portion, are preferably 1～30 weight portion.
Therefore as for what be used for the present invention's chemistry amplification photosensitive resin composition can and be the compound (C) of acid producing agent by radiation irradiation generation acid, and any compound all can use, and needing only it can be by radiation irradiation generation acid.This class acid producing agent comprises that typically those amplify the material that is used as acid producing agent in the resist usually at chemistry.Acid producing agent comprises: ion, as salt compounded of iodine, sulfonium salt, diazo salt, ammonium salt and pyridiniujm; Halide-containing is as the hydrocarbon compound of haloalkyl containing and the heterogeneous ring compound of haloalkyl containing (halogenated methyl pyrrolotriazine derivatives etc.); The diazo-ketones compound is as 1,3-diketone-2-diazo-compounds, diazobenzene naphtoquinone compounds and diazo naphthoquinone compound; Sulphones such as β-ketone sulfone and β-sulphonyl sulfone; With sulfoacid compound such as alkyl sulfonic ester, haloalkyl sulphonic acid ester, aromatic yl sulphonate and imido sulphonic acid ester.These materials can use separately, or use with two or more form of mixtures.In the present invention, with respect to 100 weight portion alkali solubility novolac resins, the common consumption of acid producing agent (C) is 0.02～10 weight portion, is preferably 0.5～3.0 weight portion.
The special preferred embodiment that is used for acid producing agent of the present invention comprises the vinyl with 2-[2-(5-methylfuran-2-yl)]-4,6-two (trichloromethyl)-s-triazine) be the cyanogen class acid producing agent of representative for the triazines acid producing agent of representative or with 5-methyl sulphonyl oxyimino group-5H-thiophene-2-subunit-2-methyl-phenylacetonitrile.
What be used for that the present invention chemistry amplifies the photosensitive resin compound contains quinone diazido photosensitizer (D), comprises the photosensitizer that contains the quinone diazido arbitrarily.For example; a kind of preferred photosensitizer, it is by making halogenation quinone di-azide sulfonic acid ester such as chlorinated naphthalene quinone di-azide sulfonic acid ester or Benzene Chloride quinone di-azide sulfonic acid ester and having and can react acquisition with low molecular weight compound or the high-molecular weight compounds that its acyl halide carries out the functional group of condensation.Can comprise hydroxyl, amino etc. with functional group's example that acyl halide carries out condensation, hydroxyl is particularly preferred.In the present invention, amplify 100 weight portion alkali soluble resins compositions in the photosensitive resin composition with respect to chemistry, the common consumption that this class contains quinone diazido photosensitizer is 1～30 weight portion, is preferably 3～15 weight portions.Amplify in the photosensitive resin composition at the present invention's chemistry, the above-mentioned quinone diazido photosensitizer that contains can use separately, or exercises usefulness with being combined into of two or more.
On the other hand, be used for alkaline soluble acrylic resin of the present invention (E), what can exemplify has: alkali solubility polyacrylate (E-1), alkali solubility polymethacrylate (E-2) and contain at least a acrylate and at least a methacrylate component units alkali solubility poly-(acrylate/methacrylate) (E-3).These acryl resins can use separately, or use with two or more array configuration.In the present invention, described alkaline soluble acrylic resin (E) can be used as required, and with respect to 100 weight portion alkali solubility novolac resins (A), its consumption is 0～200 weight portion, is generally 2～200 weight portions, is preferably 10～50 weight portions.In the present invention, the use of alkaline soluble acrylic resin provides and has improved the stable on heating effect of etchant resist.
Acryl resin preferably contains as the organic acid monomer of monomer component with at its side chain and has the acrylate of hydroxyl or methacrylate as copolymer composition, so that described resin is alkaline soluble.But, can give the alkali-soluble copolymer composition of resin and never be limited to this class organic acid monomer, or this class has the acrylate or the methacrylate of hydroxyl at its side chain.
The example that constitutes the monomer component of above-mentioned alkali solubility polyacrylate, polymethacrylate or poly-(acrylate/methacrylate) comprises: acrylate, methacrylate, organic acid monomer and other copolymerisable monomer.In the monomer component that constitutes these polymkeric substance, the example of preferred acrylate, methacrylate and organic acid monomer is as described below.
Acrylate:
Methyl acrylate, ethyl acrylate, acrylic acid n-propyl, n-butyl acrylate, the just own ester of acrylic acid, isopropyl acrylate, isobutyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, benzyl acrylate, acrylic acid-2-chloroethene ester, methyl, alpha-brominated phenyl acrylate etc.
Methacrylate:
Methyl methacrylate, Jia Jibingxisuanyizhi, n propyl methacrylate, n-BMA, the just own ester of methacrylic acid, isopropyl methacrylate, isobutyl methacrylate, the metering system tert-butyl acrylate, cyclohexyl methacrylate, benzyl methacrylate, phenyl methacrylate, methacrylic acid-1-phenyl chlorocarbonate, methacrylic acid-2-phenyl chlorocarbonate, methacrylic acid chaff ester, methacrylic acid diphenyl methyl esters, methacrylic acid pentachloro-phenyl ester, methacrylic acid naphthalene ester, isobornyl methacrylate, hydroxyethyl methylacrylate, hydroxy propyl methacrylate etc.
Organic acid monomer:
Monocarboxylic acid as acrylic acid, methacrylic acid and butenoic acid and so on; Dicarboxylic acids and its acid anhydrides as itaconic acid, maleic acid, fumaric acid, citraconic acid and mesaconic acid and so on; 2-acryloyl hydrogenated phthalates, 2-acryloyl-oxy propyl group hydrogenated phthalates etc.
In addition, other copolymerisable monomer comprises maleic acid diester, dimethyl ester, styrene and styrene derivative such as 4-fluorobenzene ethene, 2,5-difluoro styrene, 2,4-difluoro styrene, p-isopropyl styrene, chloro styrene, 4-acetophenone ethene, 4-benzoyl styrene, the 4-bromstyrol, 4-butoxy carbonyl styrene, 4-fourth oxygen methyl styrene, the 4-butylstyrene, the 4-ethyl styrene, 4-hexyl benzene ethene, the 4-methoxy styrene, the 4-methyl styrene, 2, the 4-dimethyl styrene, 2, the 5-dimethyl styrene, 2,4,5-trimethylbenzene ethene, the 4-styryl phenyl, 4-propoxyl group styrene etc., vinyl cyanide, (methyl) acrylamide, vinyl acetate, vinyl chloride, vinylidene chloride etc.As for other copolymerisable monomer, styrene and styrene derivative are preferred.These other copolymerisable monomers use as required, and its consumption can obtained within the scope of the object of the invention by described acryl resin.
The preferred embodiment that is used for the alkaline soluble acrylic resin of the present invention's chemistry amplification photosensitive resin composition comprises: a kind of a kind of being derived from (methyl) acrylic acid formation unit and/or a kind of formation unit of hydroxymethyl acrylate, a kind of formation unit and (if necessary) a kind of multipolymer that is derived from cinnamic formation unit that is derived from alkyl methacrylate of being derived from of containing; More preferably, a kind of formation unit, a kind of formation unit of methyl methacrylate, a kind of formation unit and (if necessary) a kind of multipolymer that is derived from cinnamic formation unit that is derived from n-butyl acrylate of being derived from that contains a kind of being derived from (methyl) acrylic or methacrylic acid hydroxyl ethyl ester.The average molecular weight range of acryl resin of the present invention is preferably 2000～200000, more preferably 20000～100000 (being recorded by polystyrene standard).
Amplify in the photosensitive resin composition at the present invention's chemistry, as required, use crosslinking chemical to improve film quality.In the present invention, use crosslinking chemical can improve the surfaceness of etchant resist or the reduction of film thickness.The crosslinking chemical example that is preferred for improving this class film quality comprises the compound that contains at least two kinds of ethylene oxy alkyl groups.The described preferred compound that contains at least two kinds of ethylene oxy alkyl groups for example comprises three [4-(ethylene oxy) butyl] trimellitate and two [4-(ethylene oxy) butyl] isophthalate.In the present invention, amplify 100 weight portion alkali soluble resins compositions in the photosensitive resin composition with respect to chemistry, the described consumption that contains at least two kinds of ethylene oxy alkyl group compounds is generally 0～30 weight portion, is preferably 1～10 weight portion.Amplify in the photosensitive resin composition at the present invention chemistry, but the above-mentioned compound individualism of mentioning that contains the ethylene oxy alkyl group, or exist with two or more array configurations.
In addition, amplify in the photosensitive resin composition, also can adopt other crosslinking chemical outside the above-mentioned compound of mentioning that contains the ethylene oxy alkyl group to improve film quality at the present invention chemistry.Be used to improve described other crosslinking chemical example of film quality, except melamine class crosslinking chemical, benzoguanamine class crosslinking chemical and ureas crosslinking chemical, also comprise the tetracarboxylic anhydride of alkoxyalkyl melamine resin, alkoxyalkyl carbamide resin, pyromellitic acid acid anhydride, benzophenone tetracarboxylic anhydride and tetrahydrofuran.
In photosensitive resin composition of the present invention, if desired, can introduce dyestuff, bonding agent, surfactant etc.The example of dyestuff comprises methyl violet, crystal violet, peacock green etc.The example of bonding agent comprises alkyl imidazoline, butyric acid, alkyl acid, polyhydroxy styrene, polyvinyl methyl ether, tert-butyl phenol Novolac, epoxy silane, epoxy polymer, silane etc.In addition, the example of surfactant comprises non-ionic surfactant such as polyglycol and its derivant, i.e. polypropylene glycol or polyoxyethylene lauryl ether; Fluorochemical surfactant such as Fluorad (trade name; Sumitomo 3M Co., the product of Ltd.), Megafac (trade name; Dai-Nippon Ink ﹠amp; Chemicals, the product of Inc.), Surflon (trade name; Asahi Glass Company, the product of Ltd.) and organosiloxane surfactant such as KP341 (trade name; Shin-Etsu Chemical Co., the product of Ltd.).
According to the present invention, described alkali solubility novolac resin, described self insoluble or be slightly soluble in alkali but effect by acid becomes resin that can be dissolved in alkali or compound, described acid producing agent, described quinone diazido photosensitizer, described alkaline soluble acrylic resin, described crosslinking chemical and other adjuvant that is used to improve film quality of containing, they are dissolved in the solvent with the preparation photosensitive resin composition.Be used for dissolving the examples of solvents of the constituent material of photosensitive resin composition, comprise: ethylene glycol monoalkyl ether such as glycol monomethyl methyl ether and ethylene glycol monomethyl ether; Ethylene glycol monoalkyl ether acetate such as ethylene glycol monomethyl ether acetate and ethylene glycol monomethyl ether acetate; Propylene-glycol monoalky lether such as propylene glycol monomethyl ether and propylene glycol list ethylether; Propylene-glycol monoalky lether acetic acid esters such as propylene glycol monomethyl ether and propylene glycol list ethylether acetic acid esters; Lactate such as methyl lactate and ethyl lactate; Aromatic hydrocarbons such as toluene and dimethylbenzene; Ketone such as MEK, 2-heptanone and cyclohexanone; Acid amides such as N,N-dimethylacetamide and N-Methyl pyrrolidone; Lactone such as gamma-butyrolacton; Or the like.These solvents can use separately, or use with its two or more potpourri.
What will say in passing is, the joint method in the semi-conductor packaging technology comprises: thread tacking is legal, and therein, chip is engaged to external circuit by using lead-in wire; Winding is automatically in conjunction with (TAB) method, and therein, chip is engaged on the external circuit by using metal protuberance (projection); With cover brilliant method (FC).In TAB method and two kinds of methods of FC method, all use projection formation technology, therein, projection form to be on the electrode on the chip or carry out on the electrode on the substrate.Projection normally forms by the technology that comprises following steps: barrier metal is laminated on the Silicon Wafer etc. (the LSI element is processed thereon) becomes conductive layer, a kind of photosensitive composition of coating (so-called resist) is to form photoresist on it, by mask this film is exposed, make the part that wherein forms projection be opened and be developed on this metal and form pattern, by using this pattern to adopt metalliding deposition of electrode material such as gold or copper as mould, peel this resin part off, remove barrier metal by etching, cut out a rectangular chip from a wafer, afterwards this chip is sent to structure such as TAB dress or covers the structure dress step of brilliant method etc.
Like this, in projection formed, by photosensitive resin composition, resist just was configured as a pattern form.Chemistry of the present invention amplifies photosensitive resin composition, is suitable as to contain cyanogen in these steps or do not have resist in the cyanogen electrolytic gold plating step with the preparation projection, for example, in the step that is used for preparing the gold projection.
In addition, in LSI element, the forming process of FPDs, circuit board etc. such as LCD (LCD), except projection formed, distribution etc. formed by plating.In this case, except the above-mentioned electrolytic gold plating of mentioning, copper, nickel, scolding tin or other metal all can be used as the plating material of projection and distribution etc.The present invention chemistry amplifies photosensitive resin composition, and the plating in the projection forming process or in the plating step of distribution forming process also can be preferably used as the resist that is used to form as among the step of the coating of copper, nickel, scolding tin etc.
In addition, by utilizing same corrosion-resisting pattern, this plating not only applies with individual layer but also with the continuous multi coating of two-layer or multilayer, is extensively implemented.The present invention's chemistry amplifies photosensitive resin composition, preferably as the resist in the plating step (wherein, above-mentioned electrolytic gold plating step of mentioning and copper, nickel or scolding tin plating step are carried out continuously, i.e. multilayer plating step).In addition, the order of gold-plated step in the multilayer plating or copper, nickel or scolding tin plating step can be random.
And the present invention chemistry amplifies photosensitive resin composition, also can be advantageously used for the anti-plating material in forming such as magnetic head.
Like this, the present invention's chemistry amplifies photosensitive resin composition, if desired, at first be coated on the substrate, form the substrate of conductive layer as the alloy that had adopted conductive material such as aluminium, copper, silver, gold, palladium or two or more these metals on it already, then prebake is to form the photoresist layer as thick film or super thick film.The example of this class substrate, except the aforementioned silicon substrate of mentioning, also comprise titanium nitride (TiN), nickel or permalloy (alloys of iron, nickel etc.) substrate, and soda-lime glass, quartz glass, silit, titanium carbide, zirconium carbide, borazon, aluminium nitride, silicon nitride, silicon, germanium, gallium-arsenic or gallium-phosphorus substrate, or the like.Then, said composition is carried out the pattern mode via mask and is exposed, and uses alkaline developer to develop, afterwards, and optional rinsing processing, the post exposure bake (PEB) of selectively carrying out, or the like.This will form the positive resist pattern with thick film or super thick film thickness, and it has high resolving power and excellent in shape, and it is suitable as the anti-plating material with thick film or super thick film thickness, particularly forms magnetic pole or form in the projection on magnetic head.In addition, even the anti-plating material of circuit board and use conventional positive light-sensitive resin combination other use, much less chemical-amplification positive photosensitive resin composition of the present invention, also is to be fit to use.And chemical-amplification positive photosensitive resin composition of the present invention has such as high sensitivity, the high film residual ratio in back and do not produce the premium properties of scum silica frost develops.
The present invention is used to form the method that above-mentioned photosensitive resin composition is filmed, and comprises being used to apply the conventional method that adopts of photosensitive resin composition arbitrarily, as spin-coating method, rolling method, flat method, spraying process, mobile rubbing method and the dip coated method launched of being coated with.If desired, film to adopt as silk screen print method and make.As in the used radiation of when exposure, that can enumerate has, and for example, ultraviolet ray is as g-line and i-line, far ultraviolet such as KrF excimer laser or ArF excimer laser, X-ray, electron beam, or the like.As for developing method, can use a kind of routine to be used for the method for development of photoresist, as oar formula development method, immersion development method or swing immersion development method.The example of developer comprises inorganic base such as NaOH, potassium hydroxide, sodium carbonate and sodium silicate; Organic amine such as ammonia, ethamine, propylamine, diethylamine, diethylaminoethanol and triethylamine; With quaternary amine such as tetramethylammonium hydroxide (TMAH); Or the like.
Amplify photosensitive resin composition for chemistry of the present invention, the optimal treatment condition that comprises conditions of exposure, can change according to photoresist film thickness, exposure light source, used developer etc., but, for example, when 20 μ m or thicker super thick photoresist being exposed and adopting HBO1000W/D mercury lamp (being made by Mitsubishi ElectricOsram Ltd.) (being used for following listed embodiment as exposure light source) to handle, then exposure dose is generally about 100～1000mJ/cm
2Sec.When development is that development time is about 60～900 seconds when adopting dipping or oar formula method to carry out by use organic or inorganic alkaline solution (it is through being often used as developer).
Chemistry of the present invention amplifies photosensitive resin composition and also can be used for what is called " dry film ", it be by the coating photosensitive resin composition to separable plastic foil (rather than being applied directly on the pending substrate), cure until being to form photoresist on the interim supporter and adhere formed photoresist on pending substrate such as plate at plastic foil.In addition, be used for plating solution, method for plating of the above-mentioned plating step of mentioning etc., can be known solution of any conventional or any means.
The invention advantage
The invention enables provides a kind of chemistry amplification photosensitive resin composition to become actual capabilities, for example it can reach high resolving power and high sensitivity when 10 μ m or thicker film thickness, it is being good aspect live width homogeneity that applies performance and corrosion-resisting pattern and the thermotolerance, and it can allow to form good pattern.
Embodiment
Hereinafter, will make more specific description to the present invention by embodiment, still, be limitation of the present invention in any case embodiments of the present invention can not be interpreted as.In addition, among the embodiment shown in following, " weight-average molecular weight " is the numerical value that expression is recorded by polystyrene standard.
Embodiment 1
In 200 weight portion propylene glycol monomethyl ether, dissolve 100 weight portion weight-average molecular weight and be 7000 novolac resin (40% metacresol, 60% paracresol), 30 weight portion weight-average molecular weight are that (it is by triethylene glycol and 2-ethyl butane-1 for 1000 polymkeric substance, the polycondensation reaction of 1-glycol obtains), 0.6 weight portion 2-[2-(5-methylfuran-2-yl) vinyl]-4,6-two-(trichloromethyl)-s-triazine is as acid producing agent, with 4,4 '-[1-[4-[1-(4-hydroxy phenyl)-1-Methylethyl] phenyl]-ethylidene] bis-phenol and 1,4 weight portion ester compounds of 2-naphthoquinones-(2)-diazido-4-sulfonic acid, the material that obtains is stirred, then adopt 1.2 μ m filtrators to filter, prepare photosensitive resin composition of the present invention.The composition that obtains is spun on 6 inches Silicon Wafers, and the material that obtains was cured 7 minutes in 115 ℃ on heating plate, obtains the etchant resist that thickness is 65 μ m.By exposure machine MA-200/ML (making), use HBO1000W/D mercury lamp (illumination when 405nm: 25mJ/cm by Zoom-Microtech Corp.
2Sec) (make), see through test pattern (aperture: 30～120 μ m with multiple live width by MitsubishiElectric Osram Ltd.; Wall is wide: 30～120 μ m), and to 40 seconds (1000mJ/cm of this etchant resist exposure
2), in 23 ℃ 3.0 weight %TMAH aqueous solution, developed 480 seconds, obtain corrosion-resisting pattern.Observation post gets the shape against corrosion and the film surface state of corrosion-resisting pattern.Observation is by confirming to have 60 μ m apertures and the wide pattern of 60 μ m walls carries out.The result is as shown in table 1.
The film surface state is based on that following standard judges:
⊙: rough surface and film minimizing do not exist.
Zero: observe some rough surface and film and reduce.
△: rough surface and the film of observing certain degree reduce.
*: most of etchant resist is dissolved in the developer.
Embodiment 2
Carry out the step identical with embodiment 1, difference is also to add 15 weight portion terpolymers of methacrylic acid, methyl methacrylate and n-butyl acrylate (mol ratio is 20: 50: 30) in the photosensitive resin composition of embodiment 1, its weight-average molecular weight is 30000, and the result is as shown in table 1.
Embodiment 3
Carry out the step identical with embodiment 1, difference is also to add three [4-(ethyleneoxy) butyl]-trimellitates of 1 weight portion in the photosensitive resin composition of embodiment 1, and the result is as shown in table 1.
Embodiment 4
Carry out the step identical with embodiment 1, difference is that (it is by adopting 7 times of distilled water diluting AZ 303N (KOH aqueous solution of 4.8 weight % at a kind of solution at 23 ℃, produce by Clariant (Japan) K.K.) prepare) the middle development 200 seconds, substitute at 23 ℃ and in 3.0 weight %TMAH aqueous solution pattern was developed 480 seconds, the result is as shown in table 1.
Comparative Examples 1
Carry out the step identical with embodiment 1, difference is to use a kind of like this photosensitive resin composition, it is by in 200 weight portion propylene glycol monomethyl ether, dissolve 100 weight portion weight-average molecular weight and be 7000 novolac resin (resin identical) and 2 with embodiment 1,3,4-trihydroxy-4 '-benzophenone and 1,10 weight portion ester compounds of 2-naphthoquinones-(2)-diazido-4-sulfonic acid, the result is as shown in table 1.
Comparative Examples 2
Carry out the step identical with Comparative Examples 1, difference is to use 30 weight portions, and a kind of to have weight-average molecular weight be that (it is by triethylene glycol and 2-ethyl butane-1 for 1000 polymkeric substance, the polycondensation reaction of 1-glycol obtains) substitute 2,3,4-trihydroxy-4 '-benzophenone and 1, the ester compounds of 2-naphthoquinones-(2)-diazido-4-sulfonic acid, 0.6 weight portion 2-[2-(5-methylfuran-2-yl) vinyl]-4,6-two-(trichloromethyl)-s-triazine is as acid producing agent and methacrylic acid, the 15 weight portion terpolymers (its weight-average molecular weight is 30000) of methyl methacrylate and n-butyl acrylate (mol ratio is 20: 50: 30), the result is as shown in table 1.
Comparative Examples 3
Carry out the step identical with Comparative Examples 1, difference is that (it is by adopting 7 times of distilled water diluting AZ 303N (KOH aqueous solution of 4.8 weight % at a kind of solution at 23 ℃, produce by Clariant (Japan) K.K.) prepare) the middle development 200 seconds, substitute at 23 ℃ and in 3.0 weight %TMAH aqueous solution pattern was developed 480 seconds, the result is as shown in table 1.
Table 1
| Exposure (sec.) | Thickness (μ m) | Pattern form | The film surface | Remarks | |
| Embodiment 1 | 30 | 65 | Well | ○ | Rectangle |
| Embodiment 2 | 30 | 65 | Well | ○ | Rectangle |
| Embodiment 3 | 30 | 65 | Well | ⊙ | Rectangle |
| Embodiment 4 | 30 | 65 | Well | ○ | Rectangle |
| Comparative Examples 1 | 30 | 65 | There is not resolution | △ | |
| Comparative Examples 2 | 30 | 65 | Difference | × | |
| Comparative Examples 3 | 30 | 65 | There is not resolution | △ |
The corrosion-resisting pattern that is obtained by each embodiment of the present invention does not have scum silica frost, and its shape is good.Table 1 shows that it all is good at pattern form, sensitivity and patterned surfaces state aspect that the present invention's chemistry amplifies photosensitive resin composition.And, table 1 shows, with independent use 2,3,4-trihydroxy-4 '-benzophenone and 1, the ester compounds of 2-naphthoquinones-(2)-diazido-4-sulfonic acid (it is the conventional photosensitizer that uses) is compared, and the use of acid producing agent (PAG) provides more high sensitivity and more high-resolution chemistry amplification photosensitive resin composition.This is seemingly because for the thick film situation, because conventional sensitiser absorption exposure wavelength light, the photonasty forfeiture of panel area, and the chemical amplification system that adopts PAG only needs seldom to measure the light-absorbing acid producing agent of energy, in the lithography of thick film, also can form pattern even this makes, and cause excellent in shape.And, use to contain the photosensitizer (PAC) of quinone diazido and the crosslinking chemical that is used to improve film quality of two kinds of compositions of PAG and optional selection, can guarantee that organic developer presents and the equal performance of the inorganic developer situation of use.Table 1 shows, uses PAC and two kinds of compositions of PAG and is used to improve the crosslinking chemical of film quality, and the corrosion-resisting pattern with good film surface can be provided.
Thermotolerance is estimated
The thermotolerance of being amplified the corrosion-resisting pattern that photosensitive resin composition obtains by the present invention chemistry is estimated.
Embodiment 5
The corrosion-resisting pattern that embodiment 2 obtains was heat-treated 1 minute in 90 ℃ on heating plate.Relatively not showing especially of corrosion-resisting pattern shape changes the rectangular pattern of both before and after the thermal treatment.
Embodiment 6
By carrying out the step identical, regulate embodiment 1 described photosensitive resin composition, thereby obtain corrosion-resisting pattern with embodiment 1.The film residual ratio is 98% or bigger; Pattern form is good rectangle.When the corrosion-resisting pattern that obtains at this when heat-treating like that by embodiment 5, observing pattern has microdeformation.
Previous embodiment 5 and 6 result show that in photosensitive resin composition of the present invention, the composition that contains alkaline soluble acrylic resin is good especially aspect thermotolerance.
Claims (7)
1. a chemistry amplifies photosensitive resin composition, contain: (A) alkali solubility novolac resin, (B) self is insoluble or be slightly soluble in alkali but resin or compound that effect by acid becomes and can be dissolved in alkali, (C) acid producing agent, (D) contain the photosensitizer of quinone diazido and the compound that (F) contains at least two ethylene oxy alkyl groups, the compound that wherein should (F) contains at least two ethylene oxy alkyl groups is three [4-(ethylene oxy) butyl] trimellitate or two [4-(ethylene oxy) butyl] isophthalate, and described composition (A): (B): (C): (D): weight ratio (F) is 100: 1～50: 0.5～3: 3～15: 1～10.
2. chemistry as claimed in claim 1 amplifies photosensitive resin composition, and wherein, described self insoluble or be slightly soluble in alkali but effect by acid becomes resin that can be dissolved in alkali or compound have the structural unit by following general formula (I) expression:
Wherein, R represents to have the saturated alkyl of 1～20 carbon atom, and n is 1～10 integer.
3. chemistry as claimed in claim 1 amplifies photosensitive resin composition, also contains (E) alkaline soluble acrylic resin.
4. chemical light photosensitive resin composition as claimed in claim 3, wherein, described alkaline soluble acrylic resin contains the structural unit that is derived from (methyl) acrylic acid structural unit, is derived from alkyl methacrylate, also contains if desired to be derived from cinnamic structural unit.
5. chemical light photosensitive resin composition as claimed in claim 3, wherein, described alkaline soluble acrylic resin contains the structural unit that is derived from hydroxyalkyl methacrylate, the structural unit that is derived from alkyl methacrylate, also contains if desired to be derived from cinnamic structural unit.
6. chemistry as claimed in claim 3 amplifies photosensitive resin composition, and wherein, described composition (A): (B): (C): (D): (E): weight ratio (F) is 100: 1～50: 0.5～3: 3～15: 2～200: 1～10.
7. amplify photosensitive resin composition as each described chemistry in the claim 1～6, described composition is used for the layer of 10 μ m or thicker degree.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP373069/2003 | 2003-10-31 | ||
| JP2003373069A JP4440600B2 (en) | 2003-10-31 | 2003-10-31 | Chemically amplified photosensitive resin composition for thick and ultra-thick films |
| PCT/JP2004/013354 WO2005043247A1 (en) | 2003-10-31 | 2004-09-14 | Thick film or ultrathick film responsive chemical amplification type photosensitive resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1875323A CN1875323A (en) | 2006-12-06 |
| CN1875323B true CN1875323B (en) | 2010-06-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2004800319435A Expired - Fee Related CN1875323B (en) | 2003-10-31 | 2004-09-14 | Thick film or ultrathick film responsive chemical amplification type photosensitive resin composition |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20070072109A1 (en) |
| EP (1) | EP1688793B1 (en) |
| JP (1) | JP4440600B2 (en) |
| CN (1) | CN1875323B (en) |
| AT (1) | ATE489657T1 (en) |
| DE (1) | DE602004030276D1 (en) |
| MY (1) | MY146544A (en) |
| TW (1) | TWI307825B (en) |
| WO (1) | WO2005043247A1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006134902A1 (en) | 2005-06-13 | 2006-12-21 | Tokuyama Corporation | Photoresist developer and process for producing substrate with the use of the developer |
| US7255970B2 (en) | 2005-07-12 | 2007-08-14 | Az Electronic Materials Usa Corp. | Photoresist composition for imaging thick films |
| US9436085B2 (en) * | 2009-12-16 | 2016-09-06 | Nissan Chemical Industries, Ltd. | Composition for forming photosensitive resist underlayer film |
| KR20110129692A (en) * | 2010-05-26 | 2011-12-02 | 삼성전자주식회사 | Photoresist composition and method of forming photoresist pattern using the same |
| KR20120107653A (en) | 2011-03-22 | 2012-10-04 | 삼성디스플레이 주식회사 | Photoresist resin composition and method of forming patterns by using the same |
| JP2019137612A (en) * | 2018-02-06 | 2019-08-22 | 公立大学法人大阪市立大学 | Compound, photosensitive resin composition and method for forming resist film |
| SG11202010656QA (en) * | 2018-05-24 | 2020-12-30 | Merck Patent Gmbh | Novolak/dnq based, chemically amplified photoresist |
| KR101977886B1 (en) * | 2018-06-18 | 2019-05-13 | 영창케미칼 주식회사 | Chemical amplified type positive photoresist composition for pattern profile improvement |
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- 2004-09-14 AT AT04773036T patent/ATE489657T1/en not_active IP Right Cessation
- 2004-09-14 WO PCT/JP2004/013354 patent/WO2005043247A1/en active Application Filing
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- 2004-09-14 DE DE602004030276T patent/DE602004030276D1/en active Active
- 2004-09-14 US US10/575,338 patent/US20070072109A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1688793A4 (en) | 2007-02-21 |
| DE602004030276D1 (en) | 2011-01-05 |
| MY146544A (en) | 2012-08-15 |
| TW200517782A (en) | 2005-06-01 |
| US20070072109A1 (en) | 2007-03-29 |
| CN1875323A (en) | 2006-12-06 |
| JP4440600B2 (en) | 2010-03-24 |
| ATE489657T1 (en) | 2010-12-15 |
| EP1688793B1 (en) | 2010-11-24 |
| TWI307825B (en) | 2009-03-21 |
| WO2005043247A1 (en) | 2005-05-12 |
| EP1688793A1 (en) | 2006-08-09 |
| JP2005134800A (en) | 2005-05-26 |
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